Tar ester of fatty acids and process of making same.



Farce.

HEINRICH LUDWIG DIEHL, OF DARMSTADT, GERMANY, ASSIGNOR TO DR. F. VON HEYDEN NAOIIFOLGER, OF RADEBEUL, GERMANY.

TAR ESTER OF FATTY ACIDS AND PROCESS OF MAKING SAME.

SPECIFICATION forming part of Letters Patent No. 655,208, dated August 7, 1900. Application filed September 19, 1893- Serial No. 485,871. Specimens-l To all whom it may concern:

, Be it known that I, HEINRICH LUDWIG DIEHL, doctor of philosophy, a subject of the Grand Duke of Hesse, residing at Darmstadt, in the GrandDuchy of Hesse, Germany, have invented new and useful Improvements in the Manufacture of Acid Esters of Creosote,Guai acol, and Creosol, of which the following is a specification.

This invention relates to the manufacture of acid esters ofcreosote, guaiacol, and creosol. In particular the esters of oleic acid and stearic acid are contemplated; but other acids obtainable from fatty matters can be emp1oyed--as, for example, caprylic, capric, lauric, myristic, palmitic, arachidic, ceroti c, ricinic acids, linoleic acid, erucic acid, caproic acid, and sebacic acid.

The production. of the ester is effected by the reaction under heating of dehydrating agents- -such as phosphorus trichlorid, phosphorus oxychlorid, phosphorus pentachlorid, sulphuric-chlorid, (80,01 carbon oxy-chlorid, (OOCI alkali sulfates, and the likeupon a mixture of, for example, oleic acid or stearic acid or their salts,on the one hand,with creosote, guaiacol, or creosol, or their salts, on the other hand. This process can also be carried out in two distinct phases by first causing the said chlorin compounds to act upon the said acids or salts and then causing the acid chlorid so produced to react upon the said phenols or their salts. The commercial stearic acid, which consistsof a mixture of stearic acid and palmitic acid, may be used.

The process will be rendered clear by the following example:

Eightydive parts of creosote (Pharm. Germ. III) are mixed with seventy parts of oleic acid, and to the mixture are added forty parts of phosphorus trichlorid, whereupon the mixture is gradually heated to 135 centigrade in an oil-bath. The mixture is maintained at this temperature until the production of hydrochloric-acid vapors ceases. The reaction product is freed from acids and byproducts by washing with water and is then in the form of a yellow oil of a mild pleasant flavor, reminding somewhat of creosote. It is insoluble in water, soluble with difliculty in ninety per cent. alcohol, soluble in absolute alcohol, ether, benzene, chloroform, fats,- oils, (lac. With the white or yolk of eggs or gum-arabic and water it readily forms an emulsion and is in its behavior very similar to oils. By means of alkalies it is readily saponified, more slowly by means of water or acids. From the alkaline-soap solution acids separate oil smelling strongly of creosote, which has an extraordinarily-caustic action upon mucous membranes, as it again contains free creosol together with the oleic acid.

In an analogous'manner the esters of oleic and stearic acids, on the one hand, and of guaiacol and creosol, on the other hand, are obtained. In the following the new esters of these two acids will be more particularly characterized.

I. The oleic acid-creosote-ester of beechwood-tar creosote (Ph. Germ. III) produces an oil which is insoluble in water, soluble with difficulty in ninety per cent. alcohol, and readily soluble in absolute alcohol, ether-,benzene, chloroform, disulphid. of carbon, fatty oils, &c. By the reaction of nitric acid in the presence of mercury (nascent nitrous acid) it is converted into the ester of the isomeric elaidic acid.

II. The stearic acid-creosote-ester of beechwood-tar creosote (Ph. Germ. III) is a pale yellow oil insoluble in water, soluble with difficulty in ninety per cent. alcohol, easily soluble in absolute alcohol, ether, benzin, sulphid of carbon, fatty oils, doc.

III. The oleic acid-creosote-ether from mineral coal-tar creosote is an oil insoluble in water, soluble with difficulty in ninety per cent. alcohol, readily soluble in absolute alcohol and the usual solvents of fats. By the reaction of nascent nitrous acid it is converted into the ester of elaidic acid.

IV. The stearic acidester from coal-tar is oily. It shows partially-indistinct crystallization in the cold, which, however, disappears again at ordinary temperature. It is insoluble in water, soluble with difliculty in ninety per cent. alcohol, easily soluble in the repeatedly above-named solvents of the fats.

V; The oleic acid-guaiacol ester is oily. It is transformed,like the above-mentioned oleic acid ester, into elaidic acid ester. It is ins0luble in water, soluble with difficulty in ninety yea-ate;

ber cent. alcohol,- easily soluble in absolute al- (O- -H GOORQ' erucateofi gua-iacol, creosol, 5 cohol, ether, benzin,chloroform, fatty oils, aez. and creosote, (C m -00011;) capronate of VI. The stearic acid-guaiacolester is a guaiacol, creosol, and creosote, (C H O -R;) slightly-colored oil easily soluble in absolute sepacinate of guaiacol, creosol, and creosote, alcohol, ether,'benzene, chloroform, 850,, less (O H O -R In these formulae R indicates easily in ninety per cent, alcohol,v and insolthe. guaiacol,v creosyl, and creosote radical. 5o iibl'e'in waten 7 c 7 V V H N All the said estersareoil-lilie' substances of VII. The oleicacid creosote-ester" is also" neutral reaction insoluble in water, soluble in oily. It shows, like the other oleic acid esters, alcohol and ether. All the said esters are free IO the elaid in reaction. Like the above-named fromthe intense smell and flay'or of creosote,

substances,- it is insoluble in water, soluble" guai'aciol, and creosol. They do not act caus- 55 with difficulty in ninety per cent. alcohol, ftically or burning -up0n mucous membranes easily soluble-inabsolute-alcohol,other, ben- ;flike{ these substances do, and they are inzene, disul'phid of'carbon, chloroform fatty lended to replace'them" for medicinal pur- I 5 oils, (Ste. poses; Tneyaresap onified by means of al VIII. The stearic acidcreosol ether is kalies and in the organic system; 7 V 6c oily "liquid. insoluble in water, sombre with As remedial agents the esters Era-Y vised clinical-5y in. nine y percent. alcohol, easily geitherinternatiyorextermiiyt Tn-exam soluble in the other above mentionedsol ioral l'y ws'erl' internally,beginningwitnaicare vents; or 0.1 gram.daily',.wnichmay be gradually All these esters bnil with decomposition at creased to thirty igrramst 6 temperatures ofi abou't30ir eentignade. I claimm The esters of the chic acid readily take. u 1. Tirenerein-des arib'ed process efprodiic bromi-n: under considerable heating; The i'ng non-caustic esters of high moieeal ar' 2 saponifieationisnrorediflicultwitlrthe stearic weight, insoluble in water and soluble al= acid esters than: withith'os'e of ol eic' acid cohol, ether benzin which. consists re- The gu'aiaeoh creosol; and creosote ester ct. actirrgupon fatty acidfis- W'th' leech-wood tar th'oother acids are obtained irrpreciselly the in. the presence ot acondensing agent; same: manner as in the above examples, the: '2 As a new article of mannfaetnre, a? new 30 oleic or s-tearioaeid. being replaced by e'qu'iYacaustic fatty'acid ester of bosom-Wood tar,v in

lent quantitiesof the first above-named acids soluble-in water and. soluble iii alcohol; sen- 7 5' In this way the following new bodies: areob zi n' and ethics l 1 n I V 'tained': caprylate of guaiacol, creos'ol, and -3. As anew-article ofi mamifaetwe aiiioii creosote, -H (3OOR-;)capri'nateoi guaiacol, caustic fatty acid ester. or g' u aiaeoi, insoluble.

3-.5' creosol, and creosote, (,GgH QQO'RQ 1am in watera'nd soluble in alcohol ben'zfn and nate ofi gnaiiacohe'reosol, and creosote, (to ing other; 7 v OOORt)myristiiiate'ef g'uai acol, ereosolgiaznid. testimony when-sot I have signed creosote-,1(O gH1 OOOR;.) palinritinateo-figluaia name as this specification ini the gses enee of acoli1 creosol and creosote, (GEH COOR Q two subscribing wi tnessesa 0 11 0 00119 cer'oti nat'e-of giraiacol=,lcreosol, HEINRIGHLUDWIG guaiacol,creosol, and creosote,(O H ,GOOR AUGUST WEBER, v linola-te of gu aiac'ol',creos'ol, and creosote, FRIEDRICH LQGHMAN'N. v 

